Keep 'em Up (Dean x Reader)
by Michelle-And-The-Beatle
Summary: You quite stupidly accept a challenge from Dean. Tickling. Please Enjoy! Rated T for mild kissing.


It had started out with Dean being curious about something you would rather not have him know about, leading to a challenge request, ending with you quite stupidly accepting said challenge. As if to make things worse, Dean straddled you, making sure to keep an intimate distance between you and himself. He then proceeded to voice the rules once more, clearly to make the anticipation worse for you.

"Remember, hands must stay up; keep the squirming to a minimum; feel free to smile and laugh; and most importantly, have fun," he sneers down at you. You roll your eyes, though can't hide a fond smirk at Dean's antics. Your hands were tucked under a pillow beneath your head to help minimize the chances of bringing your arms down during Dean's playful assault.

"Bring it on, tough guy," you said back to the hunter, smirking. He leans down and whispers, face inches from yours, "And if you do happen to bring those arms down, which I know you will, I get to... well, _assist_ you with it next round. Got it, sweetheart?"

You shiver but nod anyway, adding, "And if I win, you have to complete the same challenge." Dean rolls his eyes, "Alright, fine," he growled, "But there's no timer. I'll stop when I feel like it."

"Deal," you say. Dean grins back at you and says just as leisurely as when he reiterated the rules to you, "Deal."

You shift a little in your position, watching Dean carefully. But that instantly becomes a bad decision when you see his excited eyes watching yours as his fingers gently press into your sides, his digits wiggling against the soft and thin fabric of your shirt. You jolt under Dean, arms twitching at the sudden feeling, "Oho god..."

Dean smiles wider, "Be careful. I think I saw a twitch."

You shake your head, acting defiant, "N-No you dihidn't!" Dean chuckles and then quickly squeezes your hips for fun, making you buck and squeak, biting on your lower lip. You decide to shut your eyes, trying to focus on something else other than the tickling. Seeing he wasn't getting anywhere with you, Dean traces his fingers gradually higher until they knead against your lower ribs. Now a small squeak and breathy giggles escape your mouth. You start shaking your head back and forth the higher Dean's tantalizing fingers travel up your torso.

"You know I'm gonna win, don't you?" Dean says with a smirk, "And after all of this effort, you aren't gonna win," he taunts. You growl at Dean through your growing giggles. You make sure your hands are clasped in each other so they can stay up as long as possible. But each time Dean digs in between the spaces of you ribs, your arms flinch dramatically, longing to be pulled down. He continues the light touches, only using the sharp jabs to surprise you.

It takes what feels like an agonizingly long time before he's finally at the base of your underarms, where the highest ribs are. He stops moving his fingers and leaves them in that spot as you catch your breath. But you can feel that your chest is still tight from being nervous about when he would strike in that spot. All the while, Dean smiles down at you. He plants a kiss to your cheek at this point, "Think you can last any longer?"

You can't help but smile at the kiss and you say, "Oh, I'm gonna win, bud. No doubt," you raise your head confidently. Dean chuckles, "Wehe'll see." He then brings his fingers up to your biceps, wiggling them and touching the skin with the lightest touches. You squeak and your giggles come out breathy as your arms twitch dramatically. Dean smirks and trails down to your underarms and goes back up with teasing touches. You're falling for every minute of it, giggling incessantly and your arms are halfway down. Dean then stays just in your armpits and draws light circles in the hollows. Your giggling gets more frantic as he does. Then suddenly he stops and pulls away, seemingly giving you a breather. But your eyes are now closed and you let your guard down for maybe three seconds. Dean's fingers are back under your arms, this time digging in with a purpose. You shriek and your arms come shooting down to your sides, hands trying to push at Dean, "NOHOhohoho, stahaha_hahahap_!"

Dean laughed, "Ha! I knew you couldn't do it," he sang and continued wiggling his fingers unbearably under your arms, "And honestly, I'm very disappointed in you, babe. Looks like I'm gonna have to continue."

"Dehehehehehean! Stahahahahap, plehehehehease!" you laugh and squirm, head thrown back in laughter. Then Dean starts attacking every inch of your upper body he can get to, all while you're laughing hysterically. He only stops a few minutes later when your laughter goes silent and tear droplets form at the corners of your eyes. You catch your breath as Dean still straddles you.

"A-Are youhu done?" you ask. Dean chuckles and nods, "Yehes, I'm done. So, did you have fun?" he smirks. You can't help but chuckle and reach up to slap his cheek playfully, "Nohot at all, loser." Dean laughs and then leans down, pressing his lips against yours. You hum into the kiss and wrap arms around his back, fingers cascading up and down his muscles.

What do you know? Maybe this game did have its benefits for both of you.

~The End~ 


End file.
